Compound, Coating Composition Comprising Same, Organic Light-Emitting Diode Using Same, and Method for Preparing Same

ABSTRACT

The present specification relates to a compound represented by Chemical Formula 1, a coating composition comprising the compound represented by Chemical Formula 1, an organic light emitting device using the same, and a method for manufacturing the same.

TECHNICAL FIELD

This application claims priority to and the benefits of Korean PatentApplication No. 10-2017-0124472, filed with the Korean IntellectualProperty Office on Sep. 26, 2017, and Korean Patent Application No.10-2018-0109385, filed with the Korean Intellectual Property Office onSep. 13, 2018, the entire contents of which are incorporated herein byreference.

The present specification relates to a compound, a coating compositioncomprising the compound, an organic light emitting device formed usingthe coating composition, and a method for manufacturing the same.

BACKGROUND ART

An organic light emission phenomenon is one of examples convertingcurrent to visible light by an internal process of specific organicmolecules. A principle of an organic light emission phenomenon is asfollows. When an organic material layer is placed between an anode and acathode and a current is applied between the two electrodes, electronsand holes are injected to the organic material layer from the cathodeand the anode, respectively. The holes and the electrons injected to theorganic material layer recombine to form excitons, and light emits whenthese excitons fall back to the ground state. An organic light emittingdevice using such a principle may be generally formed with a cathode, ananode, and an organic material layer placed therebetween, for example,an organic material layer comprising a hole injection layer, a holetransfer layer, a light emitting layer and an electron transfer layer.

A deposition process has been normally used in the art for manufacturingan organic light emitting device. However, manufacturing an organiclight emitting device using a deposition process has a problem of highmaterial loss, and in order to resolve such a problem, technologies formanufacturing a device through a solution process capable of increasingproduction efficiency with low material loss have been developed, anddevelopment of materials usable in a solution process has been required.

Materials used in an organic light emitting device for a solutionprocess need to have properties as follows.

First, a storable homogeneous solution needs to be formed.Commercialized materials for a deposition process have favorablecrystallinity, and are not well-dissolved in a solution, or crystals arereadily caught even when forming a solution. Therefore, a concentrationgradient of the solution may change depending on the storage time orpossibility of forming a defective device is high.

Second, materials used in the solution process need to have excellentcoatability when forming a thin film so that a thin film with a uniformthickness is formed without causing holes or aggregation.

Third, layers going through the solution process need to have tolerancefor solvents and materials used in the process forming other layers, andexcellent current efficiency and excellent lifetime properties arerequired when manufacturing an organic light emitting device.

Accordingly, development of new organic materials has been required inthe art.

PRIOR ART DOCUMENTS Patent Documents

-   (Patent Document 1) Korean Patent Application Laid-Open Publication    No. 2013-106255

DISCLOSURE Technical Problem

The present specification is directed to providing a compound usable inan organic light emitting device for a solution process, and an organiclight emitting device comprising the same.

Technical Solution

One embodiment of the present specification provides a compoundrepresented by the following Chemical Formula 1.

In Chemical Formula 1,

L and L1 to L4 are the same as or different from each other, and eachindependently a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and eachindependently a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group,

R1 to R4 are the same as or different from each other, and eachindependently hydrogen; deuterium; a substituted or unsubstituted alkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup,

Y1 to Y4 are the same as or different from each other, and eachindependently —(R101)s; or —X-A, and two or more of Y1 to Y4 are —X-A,

R101 is hydrogen; deuterium; a halogen group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted alkoxy group;a substituted or unsubstituted aryl group; or a substituted orunsubstituted aryloxy group,

s is an integer of 0 to 5, and when s is 2 or greater, two or more R101sare the same as or different from each other,

X is O or S,

A is a functional group crosslinkable by heat or light,

n1 and n4 are each an integer of 0 to 4,

n2 and n3 are each an integer of 0 to 3, and

when n1 to n4 are each 2 or greater, substituents in the parentheses arethe same as or different from each other.

One embodiment of the present specification provides a coatingcomposition including the compound.

In addition, one embodiment of the present specification provides anorganic light emitting device including a first electrode; a secondelectrode; and one or more organic material layers provided between thefirst electrode and the second electrode, wherein one or more layers ofthe organic material layers include a cured material of the coatingcomposition.

Lastly, one embodiment of the present specification provides a methodfor manufacturing an organic light emitting device including preparing asubstrate; forming a first electrode on the substrate; forming one ormore organic material layers on the first electrode; and forming asecond electrode on the organic material layer, wherein the forming oforganic material layers comprises forming one or more organic materiallayers using the coating composition.

Advantageous Effects

A compound according to one embodiment of the present disclosure can beused in a solution process, and therefore, large area devices can bemanufactured. The compound can be used as a material of an organicmaterial layer of an organic light emitting device, and low drivingvoltage, high light emission efficiency and long lifetime properties canbe provided.

In addition, by forming a thin film completely cured from heat treatmentat less than 220° C. or UV treatment, the compound according to oneembodiment of the present specification forms a stable thin film notdamaged from a next solution process.

Moreover, solubility increases by using the compound of the presentdisclosure, which has an advantage of widening solvent selection whenpreparing a coating composition of a solution process.

DESCRIPTION OF DRAWINGS

FIG. 1 illustrates an example of an organic light emitting deviceaccording to one embodiment of the present specification.

MODE FOR DISCLOSURE

Hereinafter, the present specification will be described in detail.

One embodiment of the present specification provides a compoundrepresented by the following Chemical Formula 1.

In Chemical Formula 1,

L and L1 to L4 are the same as or different from each other, and eachindependently a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and eachindependently a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group,

R1 to R4 are the same as or different from each other, and eachindependently hydrogen; deuterium; a substituted or unsubstituted alkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup,

Y1 to Y4 are the same as or different from each other, and eachindependently —(R101)s; or —X-A, and two or more of Y1 to Y4 are —X-A,

R101 is hydrogen; deuterium; a halogen group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted alkoxy group;a substituted or unsubstituted aryl group; or a substituted orunsubstituted aryloxy group,

s is an integer of 0 to 5, and when s is 2 or greater, two or more R101sare the same as or different from each other,

X is O or S,

A is a functional group crosslinkable by heat or light,

n1 and n4 are each an integer of 0 to 4,

n2 and n3 are each an integer of 0 to 3, and

when n1 to n4 are each 2 or greater, substituents in the parentheses arethe same as or different from each other.

The compound according to one embodiment of the present disclosure formsa stable thin film completely cured from heat treatment or UV treatmentby comprising an oxygen (O) or sulfur (S) atom in the compound.Specifically, the compound according to one embodiment of the presentdisclosure described above has high affinity with hydrocarbon seriesand/or ether series solvents and thereby has solvent selectivity(orthogonality) by comprising an alkyl group, an alkoxy group or anaryloxy group in the compound, and may prevent migration to other layersby having tolerance for solvents used when forming layers other than anorganic material layer comprising the compound using a solution process.

In addition, excellent coatability, low driving voltage, high lightemission efficiency and long lifetime properties may be provided.

In the present specification, a description of a certain member beingplaced “on” another member comprises not only a case of the one memberadjoining the another member but a case of still another member beingpresent between the two members.

In the present specification, a description of a certain part“comprising” certain constituents means capable of further comprisingother constituents, and does not exclude other constituents unlessparticularly stated on the contrary.

In one embodiment of the present specification, the compound of ChemicalFormula 1 preferably comprises compounds having solubility for properorganic solvents.

In addition, with the compound according to one embodiment of thepresent specification, an organic light emitting device may bemanufactured using a solution coating method, and therefore, large areadevices may be manufactured.

In the present specification, the “functional group crosslinkable byheat or light” may mean a reactive substituent crosslinking compounds bybeing exposed to heat or light. The crosslinkage may be produced bylinking radicals produced while carbon-carbon multiple bonds or cyclicstructures are disintegrated by heat treatment or light irradiation.

Hereinafter, substituents of the present specification will be describedin detail.

In the present specification,

means a site bonding to other substituents or bonding sites.

The term “substitution” in the present specification means a hydrogenatom bonding to a carbon atom of a compound is changed to anothersubstituent, and the position of substitution is not limited as long asit is a position at which the hydrogen atom is substituted, that is, aposition at which a substituent can substitute, and when two or moresubstituents substitute, the two or more substituents may be the same asor different from each other.

The term “substituted or unsubstituted” in the present specificationmeans being substituted with one or more substituents selected from thegroup consisting of deuterium; a halogen group; a nitrile group; a silylgroup; a boron group; an alkyl group; a cycloalkyl group; an alkoxygroup; an aryloxy group; an aryl group; and a heterocyclic group, orbeing substituted, or being substituted with a substituent linking twoor more substituents among the substituents illustrated above, or beingunsubstituted. For example, “a substituent linking two or moresubstituents” may comprise a biphenyl group. In other words, a biphenylgroup may be an aryl group, or interpreted as a substituent linking twophenyl groups.

In the present specification, the halogen group is fluorine (F),chlorine (Cl), bromine (Br) or iodine (I).

In the present specification, the silyl group may be represented by achemical formula of —SiR_(a)R_(b)R_(c), and R_(a), R_(b) and R_(c) mayeach be hydrogen; a substituted or unsubstituted alkyl group; or asubstituted or unsubstituted aryl group. Specific examples of the silylgroup may include a trimethylsilyl group, a triethylsilyl group, atert-butyldimethylsilyl group, a vinyldimethylsilyl group, apropyldimethylsilyl group, a triphenylsilyl group, a diphenylsilylgroup, a phenylsilyl group and the like, but are not limited thereto.

In the present specification, the boron group may be represented by achemical formula of —BR_(d)R_(e), and R_(d) and R_(e) may each behydrogen; a substituted or unsubstituted alkyl group; or a substitutedor unsubstituted aryl group. Specific examples of the boron group mayinclude a trimethylboron group, a triethylboron group, atert-butyldimethylboron group, a triphenylboron group, a phenylborongroup and the like, but are not limited thereto.

In the present specification, the alkyl group may be linear or branched,and although not particularly limited thereto, the number of carbonatoms may be from 1 to 60, and according to one embodiment, the numberof carbon atoms of the alkyl group may be from 1 to 30. According toanother embodiment, the number of carbon atoms of the alkyl group isfrom 1 to 10. Specific examples of the alkyl group may include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an isobutyl group, a tert-butyl group, an n-pentyl group, ann-hexyl group, an n-heptyl group and the like, but are not limitedthereto.

In the present specification, the cycloalkyl group is not particularlylimited, but may have 3 to 60 carbon atoms, and according to oneembodiment, the number of carbon atoms of the cycloalkyl group is from 3to 40. According to another embodiment, the number of carbon atoms ofthe cycloalkyl group is from 3 to 20. Specific examples of thecycloalkyl group may include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branchedor cyclic. The number of carbon atoms of the alkoxy group is notparticularly limited, but may be from 1 to 20. Specific examples of thealkoxy group may include a methoxy group, an ethoxy group, an n-propoxygroup, an n-butoxy group, a tert-butoxy group, an n-pentyloxy group, ann-hexyloxy group, an n-octyloxy group, an n-nonyloxy group, ann-decyloxy group and the like, but are not limited thereto.

In the present specification, the aryl group is not particularlylimited, but may have 6 to 60 carbon atoms, and may be a monocyclic arylgroup or a polycyclic aryl group. According to one embodiment, thenumber of carbon atoms of the aryl group is from 6 to 30. According toone embodiment, the number of carbon atoms of the aryl group is from 6to 20. When the aryl group is a monocyclic aryl group, examples thereofmay include a phenyl group, a biphenyl group, a terphenyl group and thelike, but are not limited thereto. Examples of the polycyclic aryl groupmay include a naphthyl group, an anthracenyl group, a phenanthrenylgroup, a pyrenyl group, a perylenyl group, a triphenyl group, achrysenyl group, a fluorenyl group and the like, but are not limitedthereto.

In the present specification, the fluorenyl group may be substituted,and two substituents may bond to each other to form a spiro structure.

When the fluorenyl group is substituted, spirofluorenyl groups such as

and substituted fluorenyl groups such as

(9,9-dimethylfluorenyl group) and

(9,9-diphenylfluorenyl group) may be included. However, the structure isnot limited thereto.

In the present specification, the heterocyclic group is a heterocyclicgroup including one or more of N, O, P, S, Si and Se as a heteroatom,and although not particularly limited thereto, the number of carbonatoms may be from 2 to 60. According to one embodiment, the number ofcarbon atoms of the heterocyclic group is from 2 to 30. According toanother embodiment, the number of carbon atoms of the heterocyclic groupis from 2 to 20. Examples of the heterocyclic group may include apyridyl group, a pyrrole group, a pyrimidyl group, a pyridazinyl group,a furanyl group, a thiophene group, a benzothiophene group, a benzofurangroup, a dibenzothiophene group, a dibenzofuran group and the like, butare not limited thereto.

In the present specification, descriptions on the heterocyclic groupprovided above may be applied to the heteroaryl group except for beingaromatic.

In the present specification, descriptions on the aryl group providedabove are applied to the arylene group except for being divalent.

In the present specification, descriptions on the aryl group providedabove are applied to the aryl group in the aryloxy group.

According to one embodiment of the present specification, L is asubstituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another embodiment, L is a substituted or unsubstituted arylene grouphaving 6 to 30 carbon atoms.

According to another embodiment, L is a substituted or unsubstitutedphenylene group; or a substituted or unsubstituted biphenylylene group.When L is a substituted or unsubstituted phenylene group; or asubstituted or unsubstituted biphenylylene group, a conjugate structurethat the phenylene group or the biphenylylene group has allows an energylevel suitable for hole injection and hole transfer by enabling holes tosmoothly migrate, and a manufactured organic light emitting device haslow driving voltage, high light emission efficiency and excellentlifetime properties.

According to one embodiment of the present specification, L may berepresented by the following Chemical Formula 1-A or 1-B.

In Chemical Formulae 1-A and 1-B,

R11 to R13 are the same as or different from each other, and eachindependently hydrogen; deuterium; a substituted or unsubstituted alkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup, m1 to m3 are each an integer of 0 to 4, and when m1 to m3 are 2or greater, substituents in the parentheses are the same as or differentfrom each other.

In one embodiment of the present specification, R11 to R13 are the sameas or different from each other, and each independently hydrogen;deuterium; a substituted or unsubstituted alkyl group having 1 to 60carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20carbon atoms; a substituted or unsubstituted aryl group having 6 to 60carbon atoms; or a substituted or unsubstituted heteroaryl group having2 to 60 carbon atoms.

According to another embodiment, R11 to R13 are the same as or differentfrom each other, and each independently hydrogen; deuterium; asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms; asubstituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms; ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms.

According to another embodiment, R11 to R13 are the same as or differentfrom each other, and each independently hydrogen; deuterium; asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms; asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms; ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms.

In another embodiment, R11 to R13 are the same as or different from eachother, and each independently hydrogen; deuterium; a substituted orunsubstituted methyl group; a substituted or unsubstituted ethyl group;a substituted or unsubstituted n-propyl group; a substituted orunsubstituted n-butyl group; a substituted or unsubstituted tert-butylgroup; a substituted or unsubstituted phenyl group; a substituted orunsubstituted biphenyl group; or a substituted or unsubstituteddibenzofuran group.

According to another embodiment, R11 to R13 are the same as or differentfrom each other, and each independently hydrogen; deuterium; a methylgroup; an ethyl group; an n-propyl group; an n-butyl group; a tert-butylgroup; a phenyl group; a biphenyl group; or a dibenzofuran group.

In another embodiment, R11 to R13 are hydrogen.

According to one embodiment of the present specification, m1 to m3 areeach 0 or 1.

In one embodiment of the present specification, An and Ar2 are the sameas or different from each other, and each independently a substituted orunsubstituted aryl group having to 60 carbon atoms; or a substituted orunsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another embodiment, Ar1 and Ar2 are the same as ordifferent from each other, and each independently a substituted orunsubstituted aryl group having 6 to 30 carbon atoms; or a substitutedor unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, An and Ar2 are the sameas or different from each other, and each independently a substituted orunsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, Ar1 and Ar2 are the same as ordifferent from each other, and each independently a substituted orunsubstituted phenyl group; a substituted or unsubstituted biphenylgroup; a substituted or unsubstituted terphenyl group; or a substitutedor unsubstituted naphthyl group.

In another embodiment, Ar1 and Ar2 are the same as or different fromeach other, and each independently a phenyl group; a biphenyl group; aterphenyl group; or a naphthyl group.

In one embodiment of the present specification, R1 to R4 are the same asor different from each other, and each independently hydrogen;deuterium; a substituted or unsubstituted alkyl group having 1 to 60carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20carbon atoms; a substituted or unsubstituted aryl group having 6 to 60carbon atoms; or a substituted or unsubstituted heteroaryl group having2 to 60 carbon atoms.

According to another embodiment, R1 to R4 are the same as or differentfrom each other, and each independently hydrogen; deuterium; asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms; asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms; ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms.

In another embodiment, R1 to R4 are the same as or different from eachother, and each independently hydrogen; deuterium; a substituted orunsubstituted methyl group; a substituted or unsubstituted ethyl group;a substituted or unsubstituted phenyl group; a substituted orunsubstituted biphenyl group; a substituted or unsubstituteddibenzothiophene group; or a substituted or unsubstituted dibenzofurangroup.

According to another embodiment, R1 to R4 are the same as or differentfrom each other, and each independently hydrogen; deuterium; a methylgroup; an ethyl group; a phenyl group; a biphenyl group; adibenzothiophene group; or a dibenzofuran group.

In another embodiment, R2 and R3 are hydrogen, and R1 and R4 are aphenyl group.

In another embodiment, R1 to R4 are hydrogen.

According to one embodiment of the present specification, n1 to n4 areeach 0 or 1.

According to one embodiment of the present specification, Y1 to Y4 arethe same as or different from each other, and each independently—(R101)s; or —X-A, and two or more of Y1 to Y4 are —X-A.

In another embodiment, Y1 to Y4 are the same as or different from eachother, and each independently —(R101)s; or —X-A, and two of Y1 to Y4 are—X-A.

According to another embodiment, Y1 and Y4 are the same as or differentfrom each other, and each independently —X-A, and Y2 and Y3 are—(R101)s.

In another embodiment, Y1 and Y2 are the same as or different from eachother, and each independently —X-A, and Y3 and Y4 are —(R101)s.

According to another embodiment, Y1, Y2 and Y4 are the same as ordifferent from each other, and each independently —X-A, and Y3 is—(R101)s.

In another embodiment, Y1 to Y4 are the same as or different from eachother, and each independently —X-A.

In one embodiment of the present specification, X is O or S.

According to one embodiment of the present specification, A is afunctional group crosslinkable by heat or light.

The functional group crosslinkable by heat or light may be any one ofthe following structures.

In the structures,

T1 is hydrogen; or a substituted or unsubstituted alkyl group having 1to 6 carbon atoms, and

T2 to T4 are the same as or different from each other, and eachindependently a substituted or unsubstituted alkyl group having 1 to 6carbon atoms.

In one embodiment of the present specification, T1 is hydrogen; asubstituted or unsubstituted methyl group; a substituted orunsubstituted ethyl group; a substituted or unsubstituted n-propylgroup; a substituted or unsubstituted n-butyl group; or a substituted orunsubstituted tert-butyl group.

In another embodiment, T1 is hydrogen; a methyl group; an ethyl group;an n-propyl group; an n-butyl group; or a tert-butyl group.

According to one embodiment of the present specification, T2 to T4 arethe same as or different from each other, and each independently asubstituted or unsubstituted methyl group; a substituted orunsubstituted ethyl group; a substituted or unsubstituted n-propylgroup; a substituted or unsubstituted n-butyl group; or a substituted orunsubstituted tert-butyl group.

In another embodiment, T2 to T4 are the same as or different from eachother, and each independently a methyl group; an ethyl group; ann-propyl group; an n-butyl group; or a tert-butyl group.

According to one embodiment of the present specification, s is aninteger of 0 to 2, and when s is 2, two R101s are the same as ordifferent from each other.

In one embodiment of the present specification, R101 is hydrogen;deuterium; a halogen group; a substituted or unsubstituted alkyl grouphaving 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms; a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms; or a substituted or unsubstituted aryloxygroup having 4 to 30 carbon atoms.

In one embodiment of the present specification, R101 is hydrogen;deuterium; a halogen group; an alkyl group having 1 to 20 carbon atoms;an alkoxy group having 1 to 20 carbon atoms unsubstituted or substitutedwith an alkoxy group having 1 to 20 carbon atoms; an aryl group having 6to 30 carbon atoms; or an aryloxy group having 6 to 30 carbon atoms.

According to another embodiment, R101 is hydrogen; deuterium; fluorine(—F); a substituted or unsubstituted methyl group; a substituted orunsubstituted butyl group; a substituted or unsubstituted methoxy group;a substituted or unsubstituted ethoxy group; a substituted orunsubstituted ethylhexyloxy group; or a substituted or unsubstitutedphenyloxy group.

In another embodiment, R101 is hydrogen; deuterium; fluorine (—F); amethyl group; a butyl group; a methoxy group; an ethoxy groupunsubstituted or substituted with an alkoxy group having 1 to 20 carbonatoms; an ethylhexyloxy group; or a phenyloxy group.

According to another embodiment, R101 is hydrogen; deuterium; fluorine(—F); a methyl group; a tert-butyl group; a methoxy group; an ethoxygroup unsubstituted or substituted with an ethoxy group; a2-ethylhexyloxy group; or a phenyloxy group.

According to one embodiment of the present specification, L1 to L4 arethe same as or different from each other, and each independently asubstituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another embodiment, L1 to L4 are the same as or differentfrom each other, and each independently a substituted or unsubstitutedarylene group having 6 to 30 carbon atoms.

In another embodiment, L1 to L4 are the same as or different from eachother, and each independently an arylene group having 6 to 30 carbonatoms unsubstituted or substituted with one or more substituentsselected from the group consisting of a halogen group, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 20 carbon atoms and a substitutedor unsubstituted aryloxy group having 6 to 30 carbon atoms.

In another embodiment, L1 to L4 are the same as or different from eachother, and each independently an arylene group having 6 to 30 carbonatoms unsubstituted or substituted with one or more substituentsselected from the group consisting of a halogen group, an alkyl grouphaving 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atomsunsubstituted or substituted with an alkoxy group having 1 to 20 carbonatoms, and an aryloxy group having 6 to 30 carbon atoms.

According to another embodiment, L1 to L4 are the same as or differentfrom each other, and each independently a phenylene group unsubstitutedor substituted with one or more substituents selected from the groupconsisting of a halogen group, a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 20 carbon atoms and a substituted or unsubstitutedaryloxy group having 6 to 30 carbon atoms; or a naphthylene groupunsubstituted or substituted with one or more substituents selected fromthe group consisting of a halogen group, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 20 carbon atoms and a substituted orunsubstituted aryloxy group having 6 to 30 carbon atoms.

In another embodiment, L1 to L4 are the same as or different from eachother, and each independently a phenylene group unsubstituted orsubstituted with one or more substituents selected from the groupconsisting of fluorine (—F), a substituted or unsubstituted methylgroup, a substituted or unsubstituted tert-butyl group, a substituted orunsubstituted methoxy group, a substituted or unsubstituted ethoxygroup, a substituted or unsubstituted 2-ethylhexyloxy group and asubstituted or unsubstituted phenyloxy group; or a naphthylene groupunsubstituted or substituted with one or more substituents selected fromthe group consisting of fluorine (—F), a substituted or unsubstitutedmethyl group, a substituted or unsubstituted tert-butyl group, asubstituted or unsubstituted methoxy group, a substituted orunsubstituted ethoxy group, a substituted or unsubstituted2-ethylhexyloxy group and a substituted or unsubstituted phenyloxygroup.

According to another embodiment, L1 to L4 are the same as or differentfrom each other, and each independently a phenylene group; a naphthylenegroup; a fluorophenylene group; a methylphenylene group; adimethylphenylene group; a tert-butylphenylene group; a methoxyphenylenegroup; an ethoxyethoxyphenylene group; a phenyloxyphenylene group; or a2-ethylhexyloxyphenylene group.

According to one embodiment of the present specification, ChemicalFormula 1 may be represented by any one of the following ChemicalFormulae 2 to 5.

In Chemical Formulae 2 to 5,

R1 to R4, n1 to n4, Ar1, Ar2 and L have the same definitions as inChemical Formula 1,

X1 to X4 are the same as or different from each other, and eachindependently O or S,

A1 to A4 are the same as or different from each other, and eachindependently a functional group crosslinkable by heat or light,

R21 to R26 are the same as or different from each other, and eachindependently hydrogen; deuterium; a halogen group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted alkoxy group;a substituted or unsubstituted aryloxy group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup,

p1 and p2 are each an integer of 0 to 5,

p3 and p4 are each an integer of 0 to 4,

p5 and p6 are each an integer of 0 to 7, and

when p1 to p6 are each 2 or greater, substituents in the parentheses arethe same as or different from each other.

According to one embodiment of the present specification, R21 to R26 arethe same as or different from each other, and each independentlyhydrogen; a substituted or unsubstituted alkyl group having 1 to 20carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20carbon atoms; a substituted or unsubstituted aryloxy group having 6 to30 carbon atoms; a substituted or unsubstituted aryl group having to 30carbon atoms; or a substituted or unsubstituted heteroaryl group having2 to 30 carbon atoms.

According to another embodiment, R21 to R26 are the same as or differentfrom each other, and each independently hydrogen; fluorine (—F); asubstituted or unsubstituted methyl group; a substituted orunsubstituted tert-butyl group; a substituted or unsubstituted methoxygroup; a substituted or unsubstituted ethoxy group; a substituted orunsubstituted hexyloxy group; or a substituted or unsubstitutedphenyloxy group.

In another embodiment, R21 to R26 are hydrogen; fluorine (—F); a methylgroup; a tert-butyl group; a methoxy group; an ethoxyethoxy group; a2-ethylhexyloxy group; or a phenyloxy group.

According to another embodiment, p1 to p6 are each 0 or 1.

In one embodiment of the present specification, Chemical Formula 1 maybe represented by any one of the following Compounds 1 to 140.

The compound according to one embodiment of the present specificationmay be prepared using a preparation method to describe below.

For example, the compound of Chemical Formula 1 may have its corestructure prepared as in the following Reaction Formula 1. Substituentsmay bond using methods known in the art, and types, positions or thenumber of the substituents may vary depending on technologies known inthe art.

In Reaction Formula 1, substituents have the same definitions as thesubstituents in Chemical Formula 1.

One embodiment of the present specification provides a coatingcomposition comprising the compound of Chemical Formula 1 describedabove.

In one embodiment of the present specification, the coating compositioncomprises the compound of Chemical Formula 1 and a solvent.

In one embodiment of the present specification, the coating compositionmay be a liquid phase. The “liquid phase” means in a liquid state atroom temperature and atmospheric pressure.

In one embodiment of the present specification, examples of the solventmay comprise chlorine-based solvents such as chloroform, methylenechloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene oro-dichlorobenzene; ether-based solvents such as tetrahydrofuran ordioxane; aromatic hydrocarbon-based solvents such as toluene, xylene,trimethylbenzene or mesitylene; aliphatic hydrocarbon-based solventssuch as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane,n-octane, n-nonane or n-decane; ketone-based solvents such as acetone,methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone oracetylacetone; ester-based solvents such as ethyl acetate, butyl acetateor ethyl cellosolve acetate; polyalcohols such as ethylene glycol,ethylene glycol monobutyl ether, ethylene glycol monoethyl ether,ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol,diethoxymethane, triethylene glycol monoethyl ether, glycerin or1,2-hexanediol, and derivatives thereof; alcohol-based solvents such asmethanol, ethanol, propanol, isopropanol or cyclohexanol;sulfoxide-based solvents such as dimethyl sulfoxide; amide-basedsolvents such as N-methyl-2-pyrrolidone or N,N-dimethylformamide;tetraline, and the like, however, the solvent is not limited thereto aslong as it is a solvent capable of dissolving or dispersing the compoundof Chemical Formula 1 according to one embodiment of the presentdisclosure.

In another embodiment, the solvent may be used either alone as one type,or as a mixture mixing two or more solvent types.

In one embodiment of the present specification, the coating compositiondoes not further comprise a p-doping material.

In one embodiment of the present specification, the coating compositionfurther comprises a p-doping material.

In the present specification, the p-doping material means a materialenabling a host material to have a p semiconductor property. The psemiconductor property means a property receiving holes throughinjection or transferring holes at a highest occupied molecular orbital(HOMO) energy level, that is, a property of a material having high holeconductivity.

In one embodiment of the present specification, the p-doping materialmay be represented by any one of the following Chemical Formulae A to H,but is not limited thereto.

In the present specification, the p-doping material is not limited aslong as it has a p semiconductor property, and one, two or more typesthereof may be used, and types thereof are not limited.

In one embodiment of the present specification, a content of thep-doping material is from 0% by weight to 50% by weight based on thecompound of Chemical Formula 1.

In one embodiment of the present specification, a content of thep-doping material is from 0% by weight to 30% by weight based on a totalsolid content of the coating composition. In one embodiment of thepresent specification, a content of the p-doping material is preferablyfrom 1% by weight to 30% by weight based on a total solid content of thecoating composition, and in another embodiment, a content of thep-doping material is more preferably from 10% by weight to 30% by weightbased on a total solid content of the coating composition.

In another embodiment, the coating composition may further comprise amonomer comprising a functional group crosslinkable by heat or light; ora monomer comprising an end group capable of forming a polymer by heat.The monomer comprising a functional group crosslinkable by heat orlight; or the monomer comprising an end group capable of forming apolymer by heat as above may be a compound having molecular weight of3,000 g/mol or less.

In one embodiment of the present specification, the coating compositionhas a molecular weight of 2,000 g/mol or less, and further comprises amonomer comprising a functional group crosslinkable by heat or light; ora monomer comprising an end group capable of forming a polymer by heat.

The monomer comprising a functional group crosslinkable by heat orlight; or the monomer comprising an end group capable of forming apolymer by heat may mean a monomer in which aryl such as phenyl,biphenyl, fluorene or naphthalene; arylamine; or fluorene is substitutedwith a functional group crosslinkable by heat or light or an end groupcapable of forming a polymer by heat.

In another embodiment, the coating composition has viscosity of 2 cP to15 cP.

Satisfying the above-mentioned viscosity is advantageous inmanufacturing a device.

Another embodiment of the present specification provides an organiclight emitting device formed using the coating composition.

In one embodiment of the present specification, the organic lightemitting device comprises a first electrode; a second electrode; and oneor more organic material layers provided between the first electrode andthe second electrode, wherein one or more layers of the organic materiallayers comprise a cured material of the coating composition, and thecured material of the coating composition is in a cured state by heattreating or light treating the coating composition.

In one embodiment of the present specification, the organic materiallayer comprising the cured material of the coating composition is a holetransfer layer or a hole injection layer.

In one embodiment of the present specification, the organic materiallayer comprising the cured material of the coating composition is anelectron transfer layer or an electron injection layer.

In another embodiment, the organic material layer comprising the curedmaterial of the coating composition is a light emitting layer.

In another embodiment, the organic material layer comprising the curedmaterial of the coating composition is a light emitting layer, and thelight emitting layer comprises the compound of Chemical Formula 1 as ahost of the light emitting layer.

In another embodiment, the organic material layer comprising the coatingcomposition is a light emitting layer, and the light emitting layercomprises the compound of Chemical Formula 1 as a dopant of the lightemitting layer.

In one embodiment of the present specification, the organic lightemitting device further comprises one, two or more layers selected fromthe group consisting of a hole injection layer, a hole transfer layer.an electron transfer layer, an electron injection layer, an electronblocking layer and a hole blocking layer.

In one embodiment of the present specification, the first electrode isan anode, and the second electrode is a cathode.

According to another embodiment, the first electrode is a cathode, andthe second electrode is an anode.

In another embodiment, the organic light emitting device may be anorganic light emitting device having a structure in which an anode, oneor more organic material layers and a cathode are consecutivelylaminated on a substrate (normal type).

In another embodiment, the organic light emitting device may be anorganic light emitting device having a structure in a reverse directionin which a cathode, one or more organic material layers and an anode areconsecutively laminated on a substrate (inverted type).

The organic material layer of the organic light emitting device of thepresent specification may be formed in a single layer structure, but mayalso be formed in a multilayer structure in which two or more organicmaterial layers are laminated. For example, the organic light emittingdevice of the present disclosure may have a structure comprising a holeinjection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer, an electron injection layer and the like as theorganic material layer. However, the structure of the organic lightemitting device is not limited thereto, and may comprise less numbers oforganic material layers.

For example, a structure of the organic light emitting device accordingto one embodiment of the present specification is illustrated in FIG. 1.

FIG. 1 illustrates a structure of the organic light emitting device inwhich an anode (201), a hole injection layer (301), a hole transferlayer (401), a light emitting layer (501), an electron transfer layer(601) and a cathode (701) are consecutively laminated on a substrate(101).

FIG. 1 illustrates the organic light emitting device, however, theorganic light emitting device is not limited thereto.

When the organic light emitting device comprises a plurality of organicmaterial layers, the organic material layers may be formed withmaterials that are the same as or different from each other.

The organic light emitting device of the present specification may bemanufactured using materials and methods known in the art, except thatone or more layers of the organic material layers are formed using thecoating composition comprising the compound of Chemical Formula 1.

For example, the organic light emitting device of the presentspecification may be manufactured by consecutively laminating an anode,an organic material layer and a cathode on a substrate. Herein, theorganic light emitting device may be manufactured by forming an anode ona substrate by depositing a metal, a metal oxide having conductivity, oran alloy thereof using a physical vapor deposition (PVD) method such assputtering or e-beam evaporation, and forming an organic material layercomprising a hole injection layer, a hole transfer layer, a lightemitting layer and an electron transfer layer thereon through a solutionprocess, a deposition process or the like, and then depositing amaterial capable of being used as a cathode thereon. In addition to sucha method, the organic light emitting device may also be manufactured byconsecutively depositing a cathode material, an organic material layerand an anode material on a substrate.

In addition, one embodiment of the present specification provides amethod for manufacturing an organic light emitting device formed usingthe coating composition.

Specifically, in one embodiment of the present specification, the methodfor manufacturing an organic light emitting device comprises preparing asubstrate; forming a first electrode on the substrate; forming one ormore organic material layers on the first electrode; and forming asecond electrode on the organic material layer, wherein the forming oforganic material layers comprises forming one or more organic materiallayers using the coating composition.

In one embodiment of the present specification, the forming of one ormore organic material layers using the coating composition uses a spincoating method.

In another embodiment, the forming of one or more organic materiallayers using the coating composition uses a printing method.

In an embodiment of the present specification, examples of the printingmethod comprise inkjet printing, nozzle printing, offset printing,transfer printing, screen printing or the like, but are not limitedthereto.

The coating composition according to one embodiment of the presentspecification is suited for a solution process due to its structuralproperties and may be formed using a printing method, and therefore, iseconomically effective in terms of time and costs when manufacturing adevice.

In one embodiment of the present specification, the forming of one ormore organic material layers using the coating composition comprisescoating the coating composition on the first electrode; and heattreating or light treating the coated coating composition.

In one embodiment of the present specification, the heat treating may beperformed through heat treatment, and a heat treatment temperature inthe heat treating is from 85° C. to 250° C. According to one embodiment,the temperature may be from 100° C. to 250° C., and in anotherembodiment, the temperature may be from 150° C. to 250° C.

In another embodiment, a heat treatment time in the heat treating isfrom 1 minute to 2 hours. According to one embodiment, the time may befrom 1 minute to 1 hours, and in another embodiment, the time may befrom 30 minutes to 1 hour.

When the heat treatment or the light treatment is included in theforming of an organic material layer formed using the coatingcomposition, an organic material layer including a thin-filmed structureby a plurality of the compounds included in the coating compositionforming crosslinkage may be provided. In this case, being dissolved by asolvent or being morphologically affected or decomposed may be preventedwhen other layers are laminated on a surface of the organic materiallayer formed using the coating composition.

Accordingly, when the organic material layer formed using the coatingcomposition is formed including the heat treatment or the lighttreatment, resistance for the solvent increases, and multiple layers maybe formed by repeatedly performing solution deposition and crosslinkingmethods, and as a result, lifetime properties of a device may beenhanced by increasing stability.

As the anode material, materials having large work function are normallypreferred so that hole injection to an organic material layer is smooth.Specific examples of the anode material capable of being used in thepresent disclosure comprise metals such as vanadium, chromium, copper,zinc and gold, or alloys thereof; metal oxides such as zinc oxide,indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO);combinations of metals and oxides such as ZnO:Al or SnO₂:Sb; conductivepolymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole andpolyaniline, and the like, but are not limited thereto.

As the cathode material, materials having small work function arenormally preferred so that electron injection to an organic materiallayer is smooth. Specific examples of the cathode material comprisemetals such as barium, magnesium, calcium, sodium, potassium, titanium,indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, oralloys thereof; multilayer structure materials such as LiF/Al orLiO₂/Al, and the like, but are not limited thereto.

The hole injection layer is a layer that injects holes from anelectrode, and the hole injection material is preferably a compound thathas an ability to transfer holes, therefore, has a hole injection effectin an anode, has an excellent hole injection effect for a light emittinglayer or a light emitting material, prevents excitons generated in thelight emitting layer from moving to an electron injection layer or anelectron injection material, and in addition, has an excellent thin filmforming ability. The highest occupied molecular orbital (HOMO) of thehole injection material is preferably in between the work function of ananode material and the HOMO of surrounding organic material layers.Specific examples of the hole injection material comprise metalporphyrins, oligothiophene, arylamine-based organic materials,hexanitrile hexaazatriphenylene-based organic materials,quinacridone-based organic materials, perylene-based organic materials,anthraquinone, and polyaniline- and polythiophene-based conductivepolymers, and the like, but are not limited thereto.

The hole transfer layer is a layer that receives holes from a holeinjection layer and transfers the holes to a light emitting layer, andas the hole transfer material, materials capable of receiving holes froman anode or a hole injection layer, moving the holes to a light emittinglayer, and having high mobility for the holes are suitable. Specificexamples thereof comprise arylamine-based organic materials, conductivepolymers, block copolymers having conjugated parts and non-conjugatedparts together, and the like, but are not limited thereto.

The light emitting material is a material capable of emitting light in avisible light region by receiving holes and electrons from a holetransfer layer and an electron transfer layer, respectively, and bindingthe holes and the electrons, and is preferably a material havingfavorable quantum efficiency for fluorescence or phosphorescence.Specific examples thereof comprise 8-hydroxy-quinoline aluminumcomplexes (Alq₃); carbazole-based compounds; dimerized styryl compounds;BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole-,benzthiazole- and benzimidazole-based compounds;poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds;polyfluorene, rubrene, or the like, but are not limited thereto.

The light emitting layer may comprise a host material and a dopantmaterial.

The host material comprises fused aromatic ring derivatives,heteroring-containing compounds or the like. Specifically, the fusedaromatic ring derivative comprises anthracene derivatives, pyrenederivatives, naphthalene derivatives, pentacene derivatives,phenanthrene compounds, fluoranthene compounds and the like, and theheteroring-containing compound comprises carbazole derivatives,dibenzofuran derivatives, ladder-type furan compounds, pyrimidinederivatives and the like, however, the material is not limited thereto.

The dopant material comprises aromatic amine derivatives, styrylaminecompounds, boron complexes, fluoranthene compounds, metal complexes andthe like. Specifically, the aromatic amine derivative is a fusedaromatic ring derivative having a substituted or unsubstituted arylaminogroup and comprises arylamino group-comprising pyrene, anthracene,chrysene, peryflanthene and the like, and the styrylamine compound is acompound in which substituted or unsubstituted arylamine is substitutedwith at least one arylvinyl group, and one, two or more substituentsselected from the group consisting of an aryl group, a silyl group, analkyl group, a cycloalkyl group and an arylamino group are substitutedor unsubstituted.

Specifically, styrylamine, styryldiamine, styryltriamine,styryltetramine or the like is included, however, the styrylaminecompound is not limited thereto. In addition, the metal complexcomprises iridium complexes, platinum complexes or the like, but is notlimited thereto.

The electron transfer layer is a layer that receives electrons from anelectron injection layer and transfers the electrons to a light emittinglayer, and as the electron transfer material, materials capable offavorably receiving electrons from a cathode, moving the electrons to alight emitting layer, and having high mobility for the electrons aresuitable. Specific examples thereof comprise Al complexes of8-hydroxyquinoline; complexes comprising Alq₃; organic radicalcompounds; hydroxyflavon-metal complexes, or the like, but are notlimited thereto. The electron transfer layer may be used together withany desired cathode material as used in the art. Particularly, examplesof the suitable cathode material comprise common materials that havesmall work function, and in which an aluminum layer or a silver layerfollows. Specifically, the cathode material comprises cesium, barium,calcium, ytterbium and samarium, and in each case, an aluminum layer ora silver layer follows.

The electron injection layer is a layer that injects electrons from anelectrode, and the electron injection material is preferably a compoundthat has an ability to transfer electrons, has an electron injectioneffect from a cathode, has an excellent electron injection effect for alight emitting layer or a light emitting material, prevents excitonsgenerated in the light emitting layer from moving to a hole injectionlayer, and in addition, has an excellent thin film forming ability.Specific examples thereof comprise fluorenone, anthraquinodimethane,diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole,imidazole, perylene tetracarboxylic acid, fluorenylidene methane,anthrone or the like, and derivatives thereof, metal complex compounds,nitrogen-containing 5-membered ring derivatives, and the like, but arenot limited there.

The metal complex compound comprises 8-hydroxyquinolinato lithium,bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)berylium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium and the like, but is not limited thereto.

The hole blocking layer is a layer blocking holes from reaching acathode, and generally, may be formed under the same condition as thehole injection layer. Specifically, oxadiazole derivatives or triazolederivatives, phenanthroline derivatives, BCP, aluminum complexes and thelike are included, however, the material is not limited thereto.

The organic light emitting device according to the present specificationmay be a top-emission type, a bottom-emission type or a dual-emissiontype depending on the materials used.

Hereinafter, the present specification will be described in detail withreference to examples in order to specifically describe the presentspecification. However, the examples according to the presentspecification may be modified to various different forms, and the scopeof the present specification is not to be construed as being limited tothe examples described below. Examples of the present specification areprovided in order to more fully describe the present specification tothose having average knowledge in the art.

PREPARATION EXAMPLE Preparation Example 1. Preparation of Compound 1

1) Preparation of Intermediate 1-1

To a 500 ml round bottom flask [RBF], 2-bromo-9-phenyl-9H-fluoren-9-ol(50 g, 148.3 mmol, 1.0 eq.) and phenol (41.8 g, 444.9 mmol, 3.0 eq.)were introduced, and dissolved in methanesulfonic acid (200 ml, 0.74 M).The result was stirred overnight under reflux after installing adean-stark apparatus. After that, the reaction was stopped using asaturated aqueous NaHCO₃ solution, and the organic layer was extractedusing ethyl acetate [EA]. The organic layer was dried with magnesiumsulfate, and after removing the solvent, the result was purified usingcolumn chromatography to obtain Intermediate Compound 1-1.

2) Preparation of Intermediate 1-2

In a 500 ml round bottom flask, Intermediate 1-1 (30 g, 63.9 mmol, 1.0eq.) and cesium carbonate (41.6 g, 127.8 mmol, 2.0 eq.) were dissolvedin DMF (120 ml, 0.5 M), and then the result was stirred after raisingthe temperature to 50° C. After that, 4-vinylbenzyl chloride (9.15 ml,9.75 g, 1.0 eq.) was introduced thereto, and the result was stirred at60° C. After cooling the result to room temperature [RT], water wasintroduced thereto to stop the reaction, and then the organic layer wasextracted using ethyl acetate [EA]. The organic layer was separated,dried with magnesium sulfate, and after removing the solvent, the resultwas purified using column chromatography to obtain Intermediate Compound1-2.

3) Preparation of Compound 1

In a 250 ml round bottom flask, Intermediate 1-2 (12.0 g, 20.49 mmol,2.05 eq.), N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (3.36 g, 10.0mmol, 1.0 eq.), NaOtBu (3.36 g, 34.99 mmol, 3.5 eq.) and Pd(PtBu₃)₂ (255mg, 0.5 mmol, 0.05 eq.) were dissolved in toluene (100 ml), and theresult was stirred and reacted under N₂ charge. When the reaction wasfinished, the result was worked up with H₂O and ethyl acetate [EA], andthe organic layer was separated, dried and then filtered. After that,the solvent was removed using a rotary evaporator. The obtained crudematerial was purified using column chromatography, and after removingthe solvent, Compound 1 in a white solid form was obtained, and NMR datavalues of Compound 1 are as follows.

1H NMR (500 MHz): δ=8.00-7.82 (m, 4H), 7.70-7.68 (d, 4H), 7.62-7.55 (m,6H), 7.35-7.15 (m, 38H), 7.05-7.03 (t, 2H), 6.92-9.85 (d, 4H), 6.73-6.70(m, 2H), 5.76-5.73 (d, 2H), 5.39-5.37 (d, 2H), 5.17 (s, 4H)

Preparation Example 2. Preparation of Compound 15

1) Preparation of Intermediate 15-1

To a 500 ml round bottom flask,4-(2-bromo-9-(4-(tert-butyl)phenyl)-9H-fluoren-9-yl)phenol (50 g, 106.50mmol, 1.0 eq.), 4-bromobenzaldehyde (23.6 g, 127.8 mmol, 1.2 eq.) andpotassium carbonate (44.2 g, 319.50 mmol, 3.0 eq.) were introduced, anddissolved in dry pyridine (200 ml, 0.5 M). After that, copper(II) oxide(17.0 g, 213.0 mmol, 2 eq.) was slowly added thereto, and the reactionwas progressed under reflux after raising the temperature to 120° C.When the reaction was finished, the reaction was stopped using asaturated aqueous NaHCO₃ solution, and the organic layer was extractedusing ethyl acetate [EA]. The organic layer was dried with magnesiumsulfate, then a crude obtained by removing the solvent was dissolved indichloromethane, and by collecting precipitates in ethanol, IntermediateCompound 15-1 in a solid form was obtained.

2) Preparation of Intermediate 15-2

To a round bottom flask holding methyltriphenylphosphonium bromide(12.46 g, 34.87 mmol, 2.0 eq.), anhydrous tetrahydrofuran [anhydrousTHF] (50 ml, 0.2 M) was introduced, and the round bottom flask wasplaced into an ice bath. Potassium tert-butoxide (3.9 g, 34.87 mmol, 2.0eq.) was introduced thereto at once, and the result was stirred for 20minutes in an ice bath. Intermediate Compound 15-1 (10.0 g, 17.44 mmol,1.0 eq.) dissolved in tetrahydrofuran [THF] (30 ml) was gradually addedto the mixture using a dropping funnel. After that, while washing theround bottom flask and the funnel with tetrahydrofuran [THF] (10 ml),the rest was added. Water (50 ml) was introduced thereto to terminatethe reaction, and the organic layer was extracted using ethyl acetate[EA]. The organic layer was dried with magnesium sulfate, and afterremoving the solvent, the result was purified using columnchromatography to obtain Intermediate Compound 15-2.

3) Preparation of Compound 15

In a 250 ml round bottom flask, Intermediate Compound 15-(10.0 g, 17.50mmol, 2.05 eq.), N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (2.87 g,8.53 mmol, 1.0 eq.), NaOtBu (2.87 g, 29.86 mmol, 3.5 eq.) and Pd(PtBu₃)₂(218.0 mg, 0.43 mmol, 0.05 eq.) were dissolved in toluene (90 ml), andthe result was stirred and reacted under N₂ charge. When the reactionwas finished, the result was worked up with H₂O and ethyl acetate [EA],and the organic layer was separated, dried and then filtered. Afterthat, the solvent was removed using a rotary evaporator. The obtainedcrude material was purified using column chromatography, and afterremoving the solvent, Compound 15 in a white solid form was obtained,and NMR data values of Compound 15 are as follows.

1H NMR (500 MHz): δ=7.95-7.83 (m, 4H), 7.65-7.58 (m, 10H), 7.54-7.26 (m,22H), 7.24-7.05 (m, 12H), 6.95-6.93 (d, 4H), 6.86-6.84 (d, 4H),6.80-6.76 (m, 2H), 5.65-5.61 (d, 2H), 5.16-5.13 (d, 2H), 1.35 (s, 18H)

Preparation Example 3. Preparation of Compound 28

1) Preparation of Intermediate 28-1

To a 250 ml round bottom flask,4-(2-bromo-9-(p-tolyl)-9H-fluoren-9-yl)phenol (15 g, 35.1 mmol, 1.0eq.), potassium carbonate (14.6 g, 105.3 mmol, 3 eq.), copper(I) iodide(334.3 mg, 1.76 mmol, 0.05 eq.) and 1-butylimidazole (4.4 g, 35.1 mmol,1.0 eq.) were introduced, and dissolved in toluene (175 ml). Afterinstalling a reflux apparatus, the temperature was raised to 120° C.,and the reaction was progressed while stirring the result. When thereaction was finished, the reaction was stopped using a saturatedaqueous NaHCO₃ solution, and the result was worked up with water [H₂O]and ethyl acetate [EA]. The organic layer was separated, dried throughMgSO₄, and then filtered. After that, the solvent was removed using arotary evaporator. The obtained crude material was purified using columnchromatography to obtain Intermediate Compound 28-1.

2) Preparation of Compound 28

In a 250 ml round bottom flask, Intermediate Compound 28-(10.0 g, 18.89mmol, 2.05 eq.), N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (3.10 g,9.21 mmol, 1.0 eq.), NaOtBu (3.10 g, 32.24 mmol, 3.5 eq.) and Pd(PtBu₃)₂(235.1 mg, 0.46 mmol, 0.05 eq.) were dissolved in toluene (120 ml), andthe result was stirred and reacted under N₂ charge. When the reactionwas finished, the result was worked up with H₂O and ethyl acetate [EA],and the organic layer was separated, dried and then filtered. Afterthat, the solvent was removed using a rotary evaporator. The obtainedcrude material was purified using column chromatography, and afterremoving the solvent, Compound 28 in a white solid form was obtained,and NMR data values of Compound 28 are as follows.

1H NMR (500 MHz): δ=7.90-7.87 (m, 4H), 7.56-7.53 (m, 6H), 7.48-7.30 (m,16H), 7.27 (s, 2H), 7.25-7.22 (d, 4H), 7.20-7.15 (m, 18H), 7.14-7.12 (d,4H), 2.88 (s, 8H), 2.19 (s, 6H)

Preparation Example 4. Preparation of Compound 36

1) Preparation of Intermediate 36-1

To a 250 ml round bottom flask, Intermediate4,4′-(2-bromo-9H-fluorene-9,9-diyl)diphenol (10 g, 23.3 mmol, 1.0 eq.),potassium carbonate (9.7 g, 69.9 mmol, 3 eq.), copper(I) iodide (220.4mg, 1.17 mmol, 0.05 eq.) and 1-butylimidazole (2.9 g, 23.3 mmol, 1.0eq.) were introduced, and dissolved in toluene (100 ml). After adding3-bromobenzene (3.66 g, 23.3 mmol, 1.0 eq.) thereto, a reflux apparatuswas installed, the temperature was raised to 120° C., and the reactionwas progressed while stirring the result. When the reaction wasfinished, the reaction was stopped using a saturated aqueous NaHCO₃solution, and the result was worked up with water [H₂O] and ethylacetate [EA]. The organic layer was separated, dried through MgSO₄, andthen filtered. After that, the solvent was removed using a rotaryevaporator. The obtained crude material was purified using columnchromatography to obtain Intermediate Compound 36-1.

2) Preparation of Intermediate 36-2

To a 250 ml round bottom flask, Intermediate 36-1 (10 g, 19.78 mmol, 1.0eq.), potassium carbonate (8.20 g, 59.36 mmol, 3 eq.), copper(I) iodide(187.1 mg, 0.99 mmol, 0.05 eq.) and 1-butylimidazole (2.42 g, 19.78mmol, 1.0 eq.) were introduced, and dissolved in toluene (100 ml). Afteradding 3-bromobicyclo[4.2.0]octa-1(6),2,4-triene (3.98 g, 21.75 mmol,1.1 eq.) thereto, a reflux apparatus was installed, the temperature wasraised to 120° C., and the reaction was progressed while stirring theresult. When the reaction was finished, the reaction was stopped using asaturated aqueous NaHCO₃ solution, and the result was worked up withwater [H₂O] and ethyl acetate [EA]. The organic layer was separated,dried through MgSO₄, and then filtered. After that, the solvent wasremoved using a rotary evaporator. The obtained crude material waspurified using column chromatography to obtain Intermediate Compound36-2.

3) Preparation of Compound 36

In a 250 ml round bottom flask, Intermediate Compound 36-(10.0 g, 16.46mmol, 2.05 eq.), N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (2.70 g,8.03 mmol, 1.0 eq.), NaOtBu (2.70 g, 28.10 mmol, 3.5 eq.) and Pd(PtBu₃)₂(205.2 mg, 0.40 mmol, 0.05 eq.) were dissolved in toluene (90 ml), andthe result was stirred and reacted under N₂ charge. When the reactionwas finished, the result was worked up with H₂O and ethyl acetate [EA],and the organic layer was separated, dried and then filtered. Afterthat, the solvent was removed using a rotary evaporator. The obtainedcrude material was purified using column chromatography, and afterremoving the solvent, Compound 36 in a white solid form was obtained,and NMR data values of Compound 36 are as follows.

1H NMR (500 MHz): δ=7.88-7.85 (m, 4H), 7.57-7.55 (m, 6H), 7.52-7.30 (m,20H), 7.27-7.15 (m, 18H), 7.07-6.90 (m, 16H), 2.85 (s, 8H)

Preparation Example 5. Preparation of Compound 51

1) Preparation of Intermediate 51-1

To a 250 ml round bottom flask, 2-bromo-9H-fluoren-9-one (15 g, 57.9mmol, 1.0 eq.) and phenol (54.5 g, 579 mmol, 10.0 eq.) were introduced,and dissolved in methanesulfonic acid (70 ml, 0.8 M). The result wasstirred overnight under 60° C. After that, water was poured thereto toterminate the reaction, and then produced precipitates were filteredwhile washing with water. A precipitation process was progressed whiledropping the obtained filtered material dissolved in a small amount ofethyl acetate into hexane. The result was filtered to obtainIntermediate Compound 51-1 in a white solid form.

2) Preparation of Intermediate 51-2

In a 250 ml round bottom flask, Intermediate 51-1 (10 g, 23.29 mmol, 1.0eq.) and cesium carbonate (9.1 g, 27.95 mmol, 1.2 eq.) were dissolved indimethylformamide [DMF] (50 ml, 0.47 M), and the result was stirredafter raising the temperature to 100° C. After that, 4-ethylhexylbromide (3.71 ml, 20.96 mmol, 0.9 eq.) was slowly introduced thereto,and the result was stirred. When the reaction was finished, the resultwas cooled to room temperature [RT], water was poured thereto to stopthe reaction, and then the organic layer was extracted using EA. Theorganic layer was separated, dried with magnesium sulfate, and afterremoving the solvent, the result was purified using columnchromatography to obtain Intermediate Compound 51-2.

3) Preparation of Intermediate 51-3

To a 250 ml round bottom flask, Intermediate 51-2 (10 g, 15.5 mmol, 1.0eq.), potassium carbonate (6.4 g, 46.6 mmol, 3 eq.), copper(I) iodide(147.6 mg, 0.78 mmol, 0.05 eq.) and 1-butylimidazole (1.9 g, 15.5 mmol,1.0 eq.) were introduced, and dissolved in toluene (77 ml). Afterinstalling a reflux apparatus, the temperature was raised to 120° C.,and the reaction was progressed while stirring the result. When thereaction was finished, the reaction was stopped using a saturatedaqueous NaHCO₃ solution, and the result was worked up with water [H₂O]and ethyl acetate [EA]. The organic layer was separated, dried throughMgSO₄, and then filtered. After that, the solvent was removed using arotary evaporator. The obtained crude material was purified using columnchromatography to obtain Intermediate Compound 51-3.

4) Preparation of Compound 51

In a 250 ml round bottom flask, Intermediate Compound 51-3 (10.0 g,15.54 mmol, 2.05 eq.), N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(2.55 g, 7.58 mmol, 1.0 eq.), NaOtBu (2.55 g, 26.53 mmol, 3.5 eq.) andPd(PtBu₃)₂ (194 mg, 0.38 mmol, 0.05 eq.) were dissolved in toluene (90ml), and the result was stirred and reacted under N₂ charge. When thereaction was finished, the result was worked up with H₂O and ethylacetate [EA], and the organic layer was separated, dried and thenfiltered. After that, the solvent was removed using a rotary evaporator.The obtained crude material was purified using column chromatography,and after removing the solvent, Compound 51 in a white solid form wasobtained, and NMR data values of Compound 51 are as follows.

1H NMR (500 MHz): δ=7.90-7.85 (m, 4H), 7.55-7.52 (m, 6H), 7.48-7.26 (m,22H), 7.24-7.05 (m, 10H), 6.95-6.93 (d, 4H), 6.86-6.84 (d, 4H),3.98-3.97 (m, 2H), 3.73-3.70 (m, 2H), 2.90 (s, 8H), 1.70-1.67 (m, 2H),1.55-1.52 (m, 4H), 1.32-1.25 (m, 12H), 0.95-0.92 (t, 6H), 0.90-0.88 (t,6H)

Preparation Example 6. Preparation of Compound 65

1) Preparation of Intermediate 65-1

To a 250 ml round bottom flask,4-(2-bromo-9-(4-((2-ethylhexyl)oxy)phenyl)-9H-fluoren-9-yl)phenol (15 g,27.7 mmol, 1.0 eq.) and potassium carbonate (11.5 g, 83.1 mmol, 3 eq.)were introduced, and dissolved in DMF (150 ml). After adding3-(bromomethyl)-3-ethyloxetane (5.5 g, 30.5 mmol, 1.1 eq.) thereto, thereaction was progressed while heating and stirring the result at 70° C.When the reaction was finished, the result was worked up with H₂O andEA. The organic layer was separated, dried through MgSO₄, and thenfiltered. After that, the solvent was removed using a rotary evaporator.The obtained crude material was purified using column chromatography toobtain Intermediate Compound 65-1.

2) Preparation of Compound 65

In a 250 ml round bottom flask, Intermediate Compound 65-(10.0 g, 15.63mmol, 2.05 eq.), N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (2.56 g,7.62 mmol, 1.0 eq.), NaOtBu (2.56 g, 26.67 mmol, 3.5 eq.) and Pd(PtBu₃)₂(194.7 mg, 0.38 mmol, 0.05 eq.) were dissolved in toluene (100 ml), andthe result was stirred and reacted under N₂ charge. When the reactionwas finished, the result was worked up with H₂O and EA, and the organiclayer was separated, dried and then filtered. After that, the solventwas removed using a rotary evaporator. The obtained crude material waspurified using column chromatography, and after removing the solvent,Compound 65 in a white solid form was obtained, and NMR data values ofCompound 65 are as follows.

1H NMR (500 MHz): δ=7.91-7.95 (m, 4H), 7.56-7.53 (m, 6H), 7.45-7.20 (m,30H), 6.87-6.83 (m, 8H), 4.37-4.35 (d, 4H), 4.13-4.10 (d, 4H), 3.94-3.90(m, 2H), 3.80 (s, 2H), 3.75-3.71 (m, 2H), 1.80-1.78 (m, 2H), 1.70-1.68(q, 4H), 1.55-1.53 (m, 4H), 1.30-1.18 (m, 12H), 0.99-0.96 (t, 6H),0.88-0.84 (m, 12H)

EXAMPLE Example 1

A glass substrate on which indium tin oxide (ITO) was coated as a thinfilm to a thickness of 1,500 Å was placed in detergent-dissolveddistilled water and ultrasonic cleaned. After the ITO was cleaned for 30minutes, ultrasonic cleaning was repeated twice using distilled waterfor 10 minutes. After the cleaning with distilled water was finished,the substrate was ultrasonic cleaned with solvents of isopropyl alcoholand acetone for 30 minutes each, then dried, and then transferred to aglove box.

On the transparent ITO electrode prepared as above, a hole injectionlayer having a thickness of 300 Å was formed by spin coating a coatingcomposition mixing the following Compound 1 (20 mg), Chemical Formula D(1 mg) and toluene (1 mg), and the coating composition was cured for 1hour on a hot plate in the air. After that, the result was transferredto a vacuum depositor, and a hole transfer layer was formed by vacuumdepositing the following a-NPD on the hole injection layer.

After depositing the a-NPD to a thickness of 40 nm, the following Alq₃was vacuum deposited to 50 nm on the hole transfer layer to form a lightemitting layer. On the electron transfer layer, LiF and aluminum weredeposited to thicknesses of 0.5 nm and 100 nm, respectively, to form acathode.

In the above-mentioned process, the deposition rates of the organicmaterials were maintained at 0.4 Å/sec to 0.7 Å/sec, the depositionrates of the LiF and the aluminum of the cathode were maintained at 0.3Å/sec and 2 Å/sec, respectively, and the degree of vacuum during thedeposition was maintained at 2×10⁻⁷ to 3×10⁻⁵ torr.

Example 2

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 15 was used instead of Compound 1.

Example 3

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 28 was used instead of Compound 1.

Example 4

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 36 was used instead of Compound 1, andChemical Formula E was used instead of Chemical Formula D.

Example 5

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 51 was used instead of Compound 1, andChemical Formula E was used instead of Chemical Formula D.

Example 6

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 65 was used instead of Compound 1, andChemical Formula E was used instead of Chemical Formula D.

Example 7

An organic light emitting device was manufactured in the same manner asin Example 1 except that Chemical Formula F was used instead of ChemicalFormula D.

Example 8

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 15 was used instead of Compound 1, andChemical Formula F was used instead of Chemical Formula D.

Example 9

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 28 was used instead of Compound 1, andChemical Formula F was used instead of Chemical Formula D.

Example 10

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 36 was used instead of Compound 1, andChemical Formula G was used instead of Chemical Formula D.

Example 11

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 51 was used instead of Compound 1, andChemical Formula G was used instead of Chemical Formula D.

Example 12

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 65 was used instead of Compound 1, andChemical Formula G was used instead of Chemical Formula D.

Example 13

An organic light emitting device was manufactured in the same manner asin Example 1 except that Chemical Formula H was used instead of ChemicalFormula D.

Example 14

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 15 was used instead of Compound 1, andChemical Formula H was used instead of Chemical Formula D.

Example 15

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 28 was used instead of Compound 1, andChemical Formula H was used instead of Chemical Formula D.

Example 16

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 36 was used instead of Compound 1, andChemical Formula H was used instead of Chemical Formula D.

Example 17

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 51 was used instead of Compound 1, andChemical Formula H was used instead of Chemical Formula D.

Example 18

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 65 was used instead of Compound 1, andChemical Formula H was used instead of Chemical Formula D.

Comparative Example 1

An organic light emitting device was manufactured in the same manner asin Example 1 except that the following Compound V-1 was used instead ofCompound 1, and Chemical Formula C was used instead of Chemical FormulaD.

Comparative Example 2

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound V-1 was used instead of Compound 1,and Chemical Formula G was used instead of Chemical Formula D.

Comparative Example 3

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound V-1 was used instead of Compound 1,and Chemical Formula H was used instead of Chemical Formula D.

Comparative Example 4

An organic light emitting device was manufactured in the same manner asin Example 1 except that the following Compound V-2 was used instead ofCompound 1.

For the organic light emitting devices manufactured in Examples 1 to 18and Comparative Examples 1 to 4, driving voltage, current efficiency,quantum efficiency (QE) and luminance values were measured at currentdensity of 10 mA/cm², and time taken for the luminance decreasing to 90%compared to its initial luminance (T90) was measured at current densityof 10 mA/cm². The results are shown in the following Table 1.

TABLE 1 Driving Current Lifetime Voltage Efficiency QE Luminance T90 (10Device (V) (cd/A) (%) (Cd/m²) mA/cm²)  Example 1 3.81 5.00 5.47 499.767.2  Example 2 3.85 5.15 5.43 515.6 65.1  Example 3 3.83 5.10 5.49509.9 66.7  Example 4 3.83 5.11 5.57 510.7 70.8  Example 5 3.85 5.145.56 514.0 64.5  Example 6 3.82 5.05 5.44 498.0 65.1  Example 7 3.904.80 5.23 466.4 59.1  Example 8 3.87 5.00 5.41 505.5 65.0  Example 93.81 5.20 5.54 511.2 67.0 Example 10 3.90 4.75 4.92 455.1 55.7 Example11 3.92 4.54 5.12 447.0 48.5 Example 12 3.98 4.60 5.01 464.1 57.9Example 13 3.88 5.10 5.56 511.1 66.0 Example 14 3.90 4.88 5.31 470.365.9 Example 15 3.91 4.99 5.38 460.5 68.9 Example 16 3.93 5.21 5.60513.4 71.1 Example 17 3.81 5.12 5.61 515.0 68.7 Example 18 3.85 5.105.50 510.3 65.0 Comparative 4.04 4.25 4.60 424.7 36.3  Example 1Comparative 4.01 4.35 4.70 434.4 40.5  Example 2 Comparative 4.03 4.204.46 440.2 44.3  Example 3 Comparative 4.01 4.34 4.70 433.3 32.7 Example 4

From the results of Table 1, it was identified that Examples 1 to 18manufacturing an organic light emitting device using the compound of thepresent application had a lower driving voltage, had excellent currentefficiency and quantum efficiency, and also had excellent lifetimeproperties compared to the organic light emitting devices manufacturedin Comparative Examples 1 to 4.

REFERENCE NUMERAL

-   -   101: Substrate    -   201: Anode    -   301: Hole Injection Layer    -   401: Hole Transfer Layer    -   501: Light Emitting Layer    -   601: Electron Transfer Layer    -   701: Cathode

1. A compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1, L and L1 to L4 are the same as ordifferent from each other, and each independently a substituted orunsubstituted arylene group; Ar1 and Ar2 are the same as or differentfrom each other, and each independently a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heteroaryl group; R1 to R4are the same as or different from each other, and each independentlyhydrogen; deuterium; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted alkoxy group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup; Y1 to Y4 are the same as or different from each other, and eachindependently —(R101)s; or —X-A, and two or more of Y1 to Y4 are —X-A;R101 is hydrogen; deuterium; a halogen group; a substituted orunsubstituted alkyl group; a substituted or unsubstituted alkoxy group;a substituted or unsubstituted aryl group; or a substituted orunsubstituted aryloxy group; s is an integer of 0 to 5, and when s is 2or greater, two or more R101 s are the same as or different from eachother; X is O or S; A is a functional group crosslinkable by heat orlight; n1 and n4 are each an integer of 0 to 4; n2 and n3 are each aninteger of 0 to 3; and when n1 to n4 are each 2 or greater, R1s, R2s,R3s and R4s are the same as or different from each other.
 2. Thecompound of claim 1, wherein the functional group crosslinkable by heator light is any one of the following structures:

wherein, T1 is hydrogen; or a substituted or unsubstituted alkyl grouphaving 1 to 6 carbon atoms; and T2 to T4 are the same as or differentfrom each other, and each independently a substituted or unsubstitutedalkyl group having 1 to 6 carbon atoms.
 3. The compound of claim 1,wherein Chemical Formula 1 is represented by any one of the followingChemical Formulae 2 to 5:

wherein, in Chemical Formulae 2 to 5, R1 to R4, n1 to n4, Ar1, Ar2 and Lhave the same definitions as in Chemical Formula 1; X1 to X4 are thesame as or different from each other, and each independently O or S; A1to A4 are the same as or different from each other, and eachindependently a functional group crosslinkable by heat or light; R21 toR26 are the same as or different from each other, and each independentlyhydrogen; deuterium; a halogen group; a substituted or unsubstitutedalkyl group; a substituted or unsubstituted alkoxy group; a substitutedor unsubstituted aryloxy group; a substituted or unsubstituted arylgroup; or a substituted or unsubstituted heteroaryl group; p1 and p2 areeach an integer of 0 to 5; p3 and p4 are each an integer of 0 to 4; p5and p6 are each an integer of 0 to 7; and when p1 to p6 are each 2 orgreater, R21s, R22s, R23s, R24s, R25s and R26s are the same as ordifferent from each other.
 4. The compound of claim 1, wherein L is thefollowing Chemical Formula 1-A or 1-B:

wherein, in Chemical Formulae 1-A and 1-B, R11 to R13 are the same as ordifferent from each other, and each independently hydrogen; deuterium; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedalkoxy group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group; m1 to m3 are each aninteger of 0 to 4; and when m1 to m3 are 2 or greater, R11s, R12s andR13s are the same as or different from each other.
 5. The compound ofclaim 1, wherein Chemical Formula 1 is represented by any one of thefollowing Compounds 1 to 140:


6. A coating composition comprising the compound of claim
 1. 7. Thecoating composition of claim 6, further comprising a p-doping material.8. An organic light emitting device comprising: a first electrode; asecond electrode; and one or more organic material layers providedbetween the first electrode and the second electrode, wherein one ormore layers of the organic material layers comprise a cured material ofthe coating composition of claim
 6. 9. The organic light emitting deviceof claim 8, wherein the organic material layer comprising the curedmaterial of the coating composition is a hole transfer layer or a holeinjection layer.
 10. A method for manufacturing an organic lightemitting device comprising: preparing a substrate; forming a firstelectrode on the substrate; forming one or more organic material layerson the first electrode; and forming a second electrode on the organicmaterial layer, wherein the forming of organic material layers comprisesforming one or more organic material layers using the coatingcomposition of claim
 6. 11. The method for manufacturing an organiclight emitting device of claim 10, wherein the forming of one or moreorganic material layers using the coating composition uses a spincoating method.
 12. The method for manufacturing an organic lightemitting device of claim 10, wherein the forming of one or more organicmaterial layers using the coating composition comprises coating thecoating composition on the first electrode; and heat treating or lighttreating the coated coating composition.
 13. The compound of claim 4,wherein R11 to R13 are the same as or different from each other, andeach independently hydrogen; deuterium; a methyl group; an ethyl group;an n-propyl group; an n-butyl group; a tert-butyl group; a phenyl group;a biphenyl group; or a dibenzofuran group.
 14. The compound of claim 4,wherein m1 to m3 are each 1 or
 1. 15. The compound of claim 1, whereinAr1 and Ar2 are the same as or different from each other, and eachindependently a phenyl group; a biphenyl group; a terphenyl group; or anaphthyl group.
 16. The compound of claim 1, wherein R1 to R4 are thesame as or different from each other, and each independently hydrogen;deuterium; a methyl group; an ethyl group; a phenyl group; a biphenylgroup; a dibenzothiophene group; or a dibenzofuran group.
 17. Thecompound of claim 1, wherein n1 to n4 are each 0 or
 1. 18. The compoundof claim 1, wherein s is an integer of 0 to 2, and when s is 2, twoR101s are the same as or different from each other.
 19. The compound ofclaim 2, wherein T1 is hydrogen; a methyl group; an ethyl group; ann-propyl group; an n-butyl group; or a tert-butyl group.
 20. Thecompound of claim 2, wherein T2 to T4 are the same as or different fromeach other, and each independently a methyl group; an ethyl group; ann-propyl group; an n-butyl group; or a tert-butyl group.